Determination of barriers to rotation of axially chiral 5-methyl-2-(o-aryl)imino-3-(o-aryl)thiazolidine-4-ones
Determination of barriers to rotation of axially chiral 5-methyl-2-(o-aryl)imino-3-(o-aryl)thiazolidine-4-ones
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DOI：
10.1002/chir.22007
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发表时间：
2012-06-01
期刊：
影响因子：
2
通讯作者：
Dogan, Ilknur
中科院分区：
文献类型：
--
作者：
Erol, Sule;Dogan, Ilknur
非对映选择性地合成了热可相互转化的轴向手性5-甲基-2-（邻芳基）亚氨基-3-（邻芳基）噻唑烷-4-酮化合物，并用核磁共振氢谱确定了主要和次要对映体的构象.每个化合物的色谱分辨率已通过对映选择性高效液相色谱法进行，并通过以下的主要到次要异构体的热互变过程，直到平衡的N3-Caryl键的旋转障碍已被确定。旋转势垒的范围从96.2到115.2？kJ/mol，取决于N3-芳基环上邻位取代基的大小。Chirality 24：493498，2012. (c)2012 Wiley Periodicals，Inc.
Thermally interconvertible axially chiral 5-methyl-2-(o-aryl)imino-3-(o-aryl)-thiazolidine-4-ones have been synthesized diastereoselectively, and conformations of the major and minor enantiomeric pairs have been determined by 1H nuclear magnetic resonance. Chromatographic resolutions of each compound have been performed by enantioselective high-performance liquid chromatography, and the barriers to rotation about the N3-Caryl bond have been determined by following the thermal interconversion process of the major to minor isomers until equilibrium. The rotational barriers range from 96.2 to 115.2?kJ/mol, depending on the size of ortho substituent on N3-aryl ring. Chirality 24:493498, 2012. (c) 2012 Wiley Periodicals, Inc.